Effect of N-Alkyl chain length on the mutagenicity of N-nitrosated 1-naphthyl N-alkylcarbamates.
1-Naphthyl N-alkylcarbamates (alkyl = methyl, ethyl, n-propyl and n-butyl) were synthesized and then nitrosated with a dichloromethane extract of nitrous acid. The respective N-nitrosated carbamates were purified and tested for mutagenicity using Salmonella typhimurium LT2 strain TA98 and TA100, and Saccharomyces cerevisiae strain D3. The reactivity of the four nitrosocarbamates toward 4-(p-nitrobenzyl)-pyridine (NBP) was measured in order to assess their strengths as alkylating agents. Bioassay results indicated an inverse relationship between the length of the N-alkyl chain and the mutagenicity of the N-nitrosonaphthylcarbamates. The NBP test results indicated an inverse relationship between chemical reactivity and N-alkyl chain length.
D000478:Alkylation; D012721:Carbaryl / Q000031:analogs & derivatives* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D007306:Insecticides / Q000494:pharmacology*; D009152:Mutagenicity Tests; D009154:Mutation; D009578:Nitrobenzenes / Q000378:metabolism; D009602:Nitrosamines / Q000494:pharmacology*; D011725:Pyridines / Q000378:metabolism; D012441:Saccharomyces cerevisiae / Q000235:genetics; D012486:Salmonella typhimurium / Q000235:genetics; D013329:Structure-Activity Relationship
D007306:Insecticides; D009578:Nitrobenzenes; D009602:Nitrosamines; D011725:Pyridines; C008633:4-(4-nitrobenzyl)pyridine; C015915:1-naphthyl-N-ethyl-N-nitrosocarbamate; C015914:1-naphthyl-N-propyl-N-nitrosocarbamate; C028164:1-naphthyl-N-butyl-N-nitrosocarbamate; C008649:nitrosocarbaryl; D012721:Carbaryl